More From Succession Planning

King me: Picking your successor

Spain's King Juan Carlos I had it easy. When he decided toabdicate the throneJune 2, his successor—son Felipe, Prince of Asturias—was predetermined by law and tradition. Similarly (but less regally), many small-business owners, too, groom their offspring as the obvious choice to inherit the family firm. But larger companies, corporations and conglomerates often have a harder time sussing out just who should take over when the top dog takes off—whether retired, terminated or dead. And when that former leader is a well-known public icon whose image is intimately tied to, or conflated with, the company's, the task can be exponentially more difficult.

CNBC takes a look at five business icons whose departure—past or future—from the firms they founded, financed or finessed have either posed succession-planning headaches for shareholders and boards or spurred them to designate and insinuate their heirs themselves.